Benzoyl chloride → HCID 19826919, compound

HRID 1086159Notes

Reaction equation

HRID 1086159 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH:18]([OH:20])[CH3:19])[S:17][C:13]=2[N:12]2[C:21]([CH3:24])=[N:22][N:23]=[C:11]2[CH2:10][N:9]=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>N1C=CC=CC=1>[ClH:1].[C:25]([O:20][CH:18]([C:16]1[S:17][C:13]2[N:12]3[C:21]([CH3:24])=[N:22][N:23]=[C:11]3[CH2:10][N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:14]=2[CH:15]=1)[CH3:19])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 15135972alpha-Hydroxyetizolam

Product 1

HCID 19826919HCID 19826919, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1 g of 4-(2-chlorophenyl)-2-(1-hydroxyethyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine dissolved in 20 ml of pyridine is added 0.4 g of benzoyl chloride under ice-cooling and then stirred overnight. After completion of the reaction, the mixture is concentrated under reduced pressure and the residue is dissolved in 30 ml of ethyl acetate. The solution is washed with 5% aqueous sodium hydrogencarbonate solution and sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering off, the filtrate is concentrated under reduced pressure and the oily residue is subjected to chromatography on silica gel and eluted with chloroform-methanol (100:1-100:3). The objective fraction is concentrated under reduced pressure to give 0.4 g of 2-(1-benzoyloxyethyl)-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine.hydrochloride, melting at 180°14 193° C. with decomposition.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. concentrationthe mixture is concentrated under reduced pressure
  4. dissolutionthe residue is dissolved in 30 ml of ethyl acetate
  5. washThe solution is washed with 5% aqueous sodium hydrogencarbonate solution and sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtering off
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. washeluted with chloroform-methanol (100:1-100:3)
  10. concentrationThe objective fraction is concentrated under reduced pressure

Sources & evidence

ORD record
ord-3e0e677c8a0c44a78c3c15b64f2171b1
Source dataset
uspto-grants-1991_07
Patent number
US05028603

Reaction notes

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